Cesium carbonate → 2-[3-(3-Methoxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of methanesulfonic acid 3-(3-methoxy-phenyl)-propyl ester (1.20 g, 4.912 mmol), 4-Methyl-2-oxo-2,3-dihydro-thiazole-5-carboxylic acid ethyl ester (0.960 g, 5.128 mmol) and cesium carbonate (3.2 hm, 9.82 mmol) in anhydrous DMF was heated to oil bath at 75° C. for 2.5 h. The reaction mixture was cooled, concentrated and diluted with water (50 mL) and extracted with EtOAc (3×50 mL). The organic layers were washed with 2N HCl (30 mL), water ((30 mL), brine (30 mL), dried over magnesium sulphate, filtered and concentrated to give a brown oil. The crude product is purified by flash column chromatography (10%-30% EtOAc in hexane) to give 2-[3-(3-Methoxy-phenyl)-propoxy]-4-methyl-thiazole-5-carboxylic acid ethyl ester (0.84 g, 51%) as a yellow oil. MS m/e 336.4 (M+H+).

Provenance & Evidence